top of page

Advice: Should I Give This Guy a Second Chance?

Erin: Welcome to Hotter Than Ever Advice. I'm your host, Erin Keating, and in these short episodes I give you my opinionated and not at all officially qualified feedback about the questions, problems, quandaries and dilemmas that you have posed to me about love, sex, relationships, career, aging, ambition, divorce, and anything else that is on your mind.


Today's question is from Gabby:


"Hello Erin. I wanted to express my gratitude for inspiring me to step out of my comfort zone and meet new people. It's hard to believe that just a year ago I had convinced myself that I had lost my appeal to men. I was in a state of despair and felt unattractive due to menopause, midlife and a sexless marriage. Oh, I relate to that. However, things have taken a positive turn as I've embarked on this journey of self discovery. I've been actively engaging with men through dating apps, going on dates, and indulging in intimate encounters. Along the way, I've come to realize the value of genuine connection. While I thoroughly enjoy the physical aspect, I've started prioritizing emotional connections by investing more time in getting to know these mental before taking things further. This includes engaging in conversations over the phone, messaging, and going on casual outings like grabbing drinks or dinner. I also enjoy aftercare very much. Oh my God, me too. While it's been a fun ride so far, I want to make sure that moving forward, I am making the right decisions.


Recently, I connected with a man whom I shared a deep connection with through messaging. Our anticipation for a romantic evening was high and even though he had just arrived on a red eye flight, despite his fatigue, he expressed a strong desire to meet me. I decided to see him and we engaged in physical intimacy almost immediately. However, I was left feeling dissatisfied with the lack of emotional connection and care. Afterwards, his attempt at providing aftercare in the form of a lazy massage and some leg rubs while he watched a documentary on tv classy left me feeling empty and somewhat degraded. I did not appreciate it and it made me feel unwell. As a result, I made a firm decision to never see him again. However, he is now reaching out to me, apologizing for his behavior and expressing a sincere desire to make amends.


He promises to prove himself by lasting longer and taking better care of me. Now I'm torn about whether or not to give him a second chance. I do feel more comfortable meeting men that I've already been with than constantly going through the process with new men, but I am unsure as to whether to trust him or not. What do you think?"


Erin: Well, Gabby, congratulations. You have entered the strange and ambiguous world of dating online. There's so many incredible things about it. You can make such real connections with people in such a short amount of time. It's a very new form of intimacy.


It's a new form of connecting. And it can feel really intoxicating when you first connect with someone where you're like, oh my God, the texts are flowing. This person is interesting. He's saying all the right things. I'm engaged with him and it's kind of sexy and it's kind of flirty. We're talking about how we want to get together and we're making plans and you know, this is going to be a step on my self discovery journey. And this person seems really cool and like I'd like to spend some time with him. But sometimes things don't go as planned, you know, sometimes it's a dud.


And it sounds like your date was a dud. I do not judge you for jumping right into bed with him. It sounds like there was a lot of anticipation and it was really hot. And there's nothing like someone who's like, no, I just got off a plane, but I must see you. Like that's so attractive to be wanted in that way. And I can totally understand just going for it, right? He also went for it and he was worn out. He was not up for it. But he might have felt like if he didn't take advantage of the moment and the energy that was flowing between you in that instance that he would lose the opportunity for intimacy.


Unfortunately for him, he fucked up. And if you have a first connection like that, a first time together, the first opportunity to start off on the right foot and you're not feeling connected emotionally and they don't take care of you in bed and then afterwards they don't take care of you and it feels half assed. And he puts on a documentary on TV while you're still in the house. I hope it wasn't the History channel. I hope it wasn't a Hitler documentary, you know, I feel like he just slipped into his routine of being a single guy at the end of a night who's just gotten off and now he's tired and it's almost like you weren't even fucking there. How awful. How shitty. What a cruddy feeling.


No wonder you said you felt empty and somewhat degraded. No wonder you said it made you feel unwell. We don't want to feel like that. And as a result, you made a firm decision to never see him again. So no matter what he promises, no matter whether he says he's going to last longer and take better care of you, sweetheart, you had that chance. He had that chance. And chances are, on round two, it's not going to be any better. And if it is, it will be because he knows he fucked up and he's going to be overcompensating.


No, thanks. Let's agree to have our own backs, shall we? Let's agree to not give second chances where second chances have not been earned. Let's agree to let losers lie. Go back to your History Channel. Go back to your nature documentary. He should go back to whatever he was doing before you met him. And you should keep on moving, because if someone offers us less than what we deserve, we should not go back. Especially if we are leaving marriages where we were offered less than we deserved.


Right? I'll tell you a personal story. I met a really hot guy on Hinge, and he has a little bit of a public profile, so he posts a lot. And I really enjoyed him. He. His presence, what he did for a living. I thought he was really sexy. And we started flirting, and then it was kind of on, right? And we made a date for what was clearly only going to be sex. As much as I thought, oh, I could actually date this guy, that was not how he was thinking about me.


And I was like, all right, well, I'm hot for him, and he's definitely an interesting character who I would like to spend some time with. So I ended up going over his house, we had some wine, we talked for a long time, and then we had sex. And it was awesome. Like, the first time, it was so fun. It was so naughty. It was so connected. I really liked him. And after the first time, he sent me a nice text the next morning, and it was like, great.


You know, this is a guy who can be in my life, who is an interesting guy who I enjoy talking to and the sex is hot. Like, I will definitely see him again. So I saw him again, and after the second time, he did not send a nice note. In fact, he sent no note. It was just like, I showed up at his place, we talked for a while, we had a nice conversation, we had some wine, we had great sex. And then I didn't hear from him the next day. And I thought, this doesn't feel good. This doesn't feel good. I don't like this.


And I sent him a note saying, hey, I need to make a request of you. And my request is if we have a nice night together, I need you to send me a note and say what a nice time we had and, you know, just express some feeling, some sentiment about what it was like to be together. No big deal, no treatise. We don't need to have a letter writing romance like they did in the 1800s. I just want to be appreciated and seen and validated, and that is how I can be okay with casual sex. He was like, great, I can do that. Thank you for asking for what you need. And I was like, this is terrific. This is so mature, and I'm really proud of myself. I asked for something that I needed and I thought, this is the type of guy who I'm going to ask for these things of because he's pretty evolved and he's cool, and so that's what. He's going to do that for me.


So I saw him a third time, same drill, you know, great conversation, one glass of wine. I'm really not feeling wine these days. Hot sex, very sweet, very connected, lots of nice aftercare, all of that stuff. And as I was leaving, I got a text from him just saying, 'this was wonderful, hope to see you again soon.' I was like, great, I asked for the note. He gave me the note. I'm getting my needs met.


This is all I really need in this dynamic. The fourth time we're together, same thing, no note, no note. In the morning, I looked at my phone hoping to see something from him, and there was nothing. And I sent him a note. And I said, remember how I asked for you to send me a note? I mean, this is like, how little could I fucking ask for in this scenario, right? And he can't even send me a text. And he said, thanks so much. You did ask for that. Thanks for expressing yourself and not carrying resentment.


But he did not apologize. He did not say, oh, yes, I agreed to do that. I agreed to do that and I didn't do that, and I'm sorry. And then I decided I was done. Because if I am going to have a casual connection, I need to feel like you give a shit. I am really special. I am really fucking awesome. I may be willing to have casual sex, but I am not willing to be treated poorly. And I am not willing to ask for one small thing and have you not give me that one small thing.


You know what that says to me is I care about you less than that one small thing you asked for. I don't care about you. So I am willing to take advantage of what you are offering and I can be present in the moment and it can be nice, but the second you are gone, I do not think about you. And I just, I unfollowed him on social media and I decided like, no, this is not a guy who gets to be in my life. It's a bummer because in the abstract, the idea of him, to quote a Anne Hathaway movie recently reviewed on this here podcast, the idea of him was wonderful. The idea of your, you know, I just ran off my flight and had to see you guy who you connected with so well over text, but not in real life. Mr.


I need to watch a documentary where I give you a half assed leg rub. We're worth more than that. And if you have that yucky feeling and you walk back into that situation and set yourself up for that yucky feeling again, that's on you. That's on you. And you wouldn't wish that yucky feeling on your friends or on anyone you cared about. I would say practice having your own back. You know, for me, it took a minute to decide to practice having my own back. And he was able to follow through on that once or twice.


But I mattered so little to him that he couldn't even send me a text, I'm worth more than that. And I just had to say that to myself, you're worth more than this. There are plenty of fish in the sea. There are so many guys who are good at sex, who will make you feel good, who you can have a nice conversation with and who will chase you and be interested in you and compelled by you. And that's what you deserve. You want that emotional connection. You want to feel like someone cares, even in a casual context. You know, a genuine connection is what you value.


So continue to prioritize those emotional connections. Maybe go out with someone before you go straight into intimacy. Sometimes going straight into intimacy is hot and great and fun. And sometimes it helps to build the anticipation and to strengthen whatever was there on text into something a little bit meatier. I'm not talking about the love of our lives here. I'm just talking about you and he. Acknowledging that both of you are worthwhile, worth getting to know, worth each other's time, and that you're taking care of what it is that you need in this period of discovery and exploration in your life.


Gabby, I don't know you and I don't know what your marriage was like, but I'm willing to bet that if it has dissolved to the place where you're both seeing other people and you're both Kind of dipping your toes in a new life. I am willing to bet that your marriage was a place where you didn't get your needs met. And in this phase of your life, dating is a great place to practice saying what you want, saying what your deal breakers are, saying what your needs are and just putting that out there and living with the consequences of getting those needs met or not getting them met. And if you don't get them met, move on, because otherwise we end up in relationships where we are not valued, casual or otherwise.


We end up letting ourselves be treated in a way that that doesn't make us feel good. You know, you can be interested in these loose ties and still have standards and still have needs and they are not going to be the needs that you have in a long term committed relationship. But I think all of these dating experiences are great ways to build muscle, great ways to practice taking care of ourselves and asking to have our needs met. And then when we don't get our needs met, moving on and not spending too much time worrying about this one guy or that one guy, especially if they weren't great in bed.


You take care of you. You take care of you, and you pursue the men who pursue you in the way that feels the best to you in this moment in your life. It's okay. You might need to kiss some more frogs. And none of them is going to be Prince Charming, but some of them are going to be great. Some of them are going to be people you want to spend time with and maybe that's all the relationship ends up being and maybe the relationship becomes something else. And it doesn't really matter because we are not 20 years old looking to get married and have babies. We're not kids, we're fucking grown ass women. We deserve to be treated as such. Thank you Gabby. I wish you all the best.


Thanks for listening to Hotter Than Ever advice. How can you ask a question? I'm so glad you asked, DM us @hotterthaneverpod on Instagram or leave me a voicemail or text the Hotter Than Ever Hottie Hotline at 323-844-2303. I would love to answer your question in a future episode.


Hotter Than Ever is produced by Erica Gerard and Podkit Productions. Our associate producer is Melody Carey with music by Chris Keating and vocals by Issa Fernandez.

Comments


bottom of page